Azo dye.



HEINRICH- JORDAN AND WIL} ELM NEELMEIER, or nnvnakiisnn, NEAR COLOGNE,GERMANY, ASSIGNORS T ARBENFABRIKEN VORM FRI'EDR'. BAYER & 00., orELBERFELD,'GERMANY, A UORPOR-ATION oFo RMANY.

AZO DYE. 1,02%080. p fi a of Letters Patent Patented Apr. 23, 1912. NoDrawing.' Application filed November 10, 1911.

To all whom, it may concern:

- Be it known that we, HEINRICH JORDAN and lVILHELM NEELMEIER, .doctorsof phi lo'sophy, chemists,

Empire, residing at Leverkusen near Cologne, Germany, have invented newand useful Improvements in the following is a specification. Greensubstantive dyestuffs capable of further diazotization have hitherto notbeen obtained, though they would be of a great technical value as ber ofcoloring matters of such character already known or of modifying theshades pr0duced from the latter. lVe have now succeeded in preparingdyes of this character capable of dyeing cotton in green togreenish-blue shades. The process for their 4 production consistsincombining diazo compounds of acidylpara-diamins, such asacidyl-para-phenylenediamins, acidyl-lA- naphthylenediamins with asuitable middle componentwhich can be further diazotized after thecombination. The aminoazo com- :5 pounds thus obtained are againdiazotized and combined with 2-amino-8-naphthol-6- sulfonic acid; theresulting aminodisazo coloring matters are diazotized,- coupled with apyrazol'one andthe trisazo dyestuffs thus 0 obtained are finallysaponified. The same results are obtained on using in this processinstead of acidyl-para-phenylenediamins or ofacidyl-1.4-naphthylenediamins or of derivatives of these compounds thecorre- 5 sponding nitroamino compounds and on finally reducing thenitrogroup contained in the trisazo dyestuffs, instead of elim.-.1 ating theacidyl' group contained in the trisazo dyestuffs if prepared as beforedescribed.

) The new dyestu'fi's areafter being dried and pulverized in the shapeof their alkaline salts dark powders soluble in water. Upon reductionwith stannous chlorid and hydrochloric acid they yield a para-diamin,

i a diamin, 2.7-diamino-8-oxynaphthalene-6- sulfonic acid and anamino-pyrazolone. They dye cotton in green to greenish-blue shades,which on being diazotized and decitizens of the German- Azo Dye, (ifwhich an addition to the num- Serial No. 659,571.

produce dyeings very to light, and capable with hydrosulfite to a verypure white.

In order to illustrate the new process more fully the following exampleis given. the parts being by weight :230 parts ofamino--acetylaminobenzne-Q-sulfonic acid are dissolved in 7000 parts ofwater and 55 p'arts'of soda. The solution is acidulated with 280 partsof hydrochloric acid and diazotized with 69 'arts of sodium nitrite atfrom 15 to 20 The diazo compound is combined with a solution of 245parts of the sodium salt of 1.6-naphthylamin sulfonic acid containing250 parts of sodium acetate. The combination is finished after stirringfor a short time. The solution is then acidufast to washing and of beingdischarged of 19 B. and diazotize'd with 69 parts of sodium nitrite atfrom 1015 C. stirring for about 1 hour the diazotization is to run intoa solution of 261 parts of the sodium salt of2-amino8-naphthol-6-sulf0nic acid and 800 parts of soda. The coupling issoon finished. The disazo dyestuff is separated by the addition of saltand filtered off. It is well mixed with 7000 parts of water; 600 partsof hydrochloric acid are added to the paste and the-mixture is cooled to0 and diazotized with 69 parts of sodium nitrite. It is stirred untilthe nitrite reaction has disappeared and the diazo compound is thenallowed to run into a solution kept at a temperature of 10 C. of 174.-parts of phenylmethylpyrazolone in 3000 parts of water and 700 parts ofsoda. After stirring for 1 hour it is heated to 60 C. and the dyestuflis salted out and filtered. The paste is introduced into 3000 parts ofwater and the mixture heated to boiling. 1400 parts of soda lye isneutralized with a mineral acid and the saponified dyestufi' iscollected on a filter;

of soda lye per cent. NaOH) are then added and the boiling is continuedfor hour. After cooling to (SO-70 C. the excess l veloped" on the fibere. g. with beta-naphthol lated with 700 parts of hydrochloric acid Aftercomplete and the diazo compound is allowed SOSH is after being dried andpulverized in the shape of its sodium salt a dark powder. Itdissolves'in water with a pure green color and dyes cotton directly inbluish-green shades, which when diazotized and developed withbeta-napht-hol turn into slightly bluer shades of excellent fastness towash: ing and to light. Upon reduction with stannous chlorid andhydrochloric acid itis split up into 1.l-phenylenediamin-Q-sulfonicacid, 1.l-naphthylenediamin-6-sulfonic acid,2.7 diamino- 8 -oxynaphthalene-G-sulfonic acid and 1 phenyl 3methyl--aminm5-pyrazolone.

lVe claim e 1. The herein described new dyestufis which are after beingdried and pulverized in the shape of their alkaline salts dark powderssoluble in water; yielding upon reduction in the shape of its sodiumsalt a dark powder soluble in water with a pure green color; yieldingupon reduction with stannous chlorid andhydrochloric acid1.4l-phenylenediamin-G-sulfo'nic acid, l.4-naphthylenediamin- G-sulfonicacid 2.T-diamino-8oxynaphthalene-dsulfonic acid and1phenyl-3-methyll-an1ino-5pyrazolone: dyeing cotton --:li-

rectlyin bluish-green shadeswhich when diazotized and developed withbeta-naphthol turn into slightly bluer shades of excellent fastncss towashing and to light and capable of lacing discharged with hydrosulfiteto a very pure white, substantially as described.

In testimony whereof we have hereunto set our hands in the presence oftwo sub scribing witnesses.

HEINRICH JORDAX. 5. WILHELM NEELMEIER. [Ls] lVitnesses HELEN Norm,ALBnnr NUFER.

